Isopropyl iodide → HCID 68746443, compound

HRID 1864781Notes

Reaction equation

HRID 1864781 reaction equation
[F:1][C:2]1[CH:52]=[CH:51][C:5]([C:6]([N:8]([CH2:15][C:16]2[CH:21]=[C:20]([C:22]3[CH:49]=[CH:48][C:25]4[N:26]([C:29]([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[N:27]=[N:28][C:24]=4[CH:23]=3)[CH:19]=[CH:18][C:17]=2[F:50])[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1.[CH:53](I)([CH3:55])[CH3:54].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]([CH2:15][C:16]2[CH:21]=[C:20]([C:22]3[CH:49]=[CH:48][C:25]4[N:26]([C:29]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)([C:42]5[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=5)[C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[N:27]=[N:28][C:24]=4[CH:23]=3)[CH:19]=[CH:18][C:17]=2[F:50])[CH:9]2[CH2:14][CH2:13][N:12]([CH:53]([CH3:55])[CH3:54])[CH2:11][CH2:10]2)=[O:7])=[CH:51][CH:52]=1

Participants

6

Reactant 3

HCID 6362Isopropyl iodide2×HCID 11430Potassium CarbonateHCID 68750976HCID 68750976, compound

Product 1

HCID 68746443HCID 68746443, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-Fluoro-N-[2-fluoro-5-(1-trityl-1H-benzotriazol-5-yl)-benzyl]-N-piperidin-4-yl-benzamide (25 mg, 0.04 mmol), isopropyl iodide (34 mg, 0.2 mmol) and potassium carbonate (28 mg, 0.2 mmol) in 2 mL of DMF was heated at 40° C. for 3 h when additional isopropyl iodide (34 mg, 0.2 mmol) was added. The mixture was heated for an additional 2 h and then left at ambient temperature for 10 days. The mixture was diluted with water and the product extracted into ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated to leave the crude product. Chromatography (elution with methanol/dichloromethane) provided 18 mg of product.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated for an additional 2 h
  3. extractionthe product extracted into ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto leave the crude product
  8. washChromatography (elution with methanol/dichloromethane)

Sources & evidence

ORD record
ord-f2c10accf11d4fdd8f235da3e77bcbae
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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